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In late 1953, in a modest flat tucked away on the southside of Chicago, one of the most controversial, pioneering and sexually liberal magazines ever to hit newsstands was born.

Playboy, whose founder Hugh Hefner died today aged 91, was the gospel of responsibility-free, erotically-charged, hedonistic bachelorhood. The magazine was conceived as a remedy for post-war sexual repression in the US. Hefner’s fascination with Alfred Kinsey’s Sexual Behavior in the Human Male, and his puritanical upbringing in midtown America, inspired the first copy of the seminal ‘men’s mag’.

Hefner took out a bank loan and managed to raise $8,000 from 45 investors - including his mum. He released the first issue of Playboy - originally called Stag Party - with Marilyn Monroe on the cover and a nude centrefold of the starlet inside. It sold an impressive 50,000 copies, signalling a seismic shift within a male readership yearning for more barefaced (or bare-bottomed) sex between its pages.

Playboy founder Hugh Hefner (Photo by Robert Mora/Getty Images)

For all his titillation and worship of big breasts and blonde hair, Hefner was also a far more complex character than is often represented. Playboy wasn’t only a fetishistic gaze at the female nude; it had substance and style. Hefner was able to mix high culture with glossy sex in a way not seen before. He commissioned prominent writers such as John Steinbeck, Tennessee Williams, John Updike, Gore Vidal, Arthur C. Clarke and Philip Roth for interviews and articles. The magazine staunchly advocated racial equality and reproductive rights - Playboy published content from black activists like Martin Luther King Jr. and Malcolm X, and was one of the first magazines to have a black woman on its cover. This was no one-trick pony.

Playboy and Hefner's vision for post-war America was aspirational too. The sexual revolution after two devastating conflicts hadn't materialised in the way he thought it would. Liberation, for The Hef, was marked by supple leather armchairs, high-end liquor and sexually loose women. Hefner wrote in his first editor's note, his vision for Playboy was ‘mixing up cocktails and an hors d'oeuvre or two, putting a little mood music on the phonograph and inviting in a female for a quiet discussion on Picasso, Nietzsche, jazz, sex.’ And that’s exactly what it did. Hefner created an image of a well-read, well-dressed eligible bachelor whose thirst for culture was as deep as his thirst for sex. And by the 1970s, the magazine was selling over seven million copies a month worldwide.

But for all the editorial triumphs of this deeply masculine ideology, the life and work of The Hef is harder to reconcile under a feminist lens. While his pro-sex 'revolution' (if you want to call it that) may have helped paved the way for a more open, robust and explicit dialogue about sexuality, his incessant objectification of women both in public and private life was incredibly problematic. The Playboy Mansion, and Hefner’s private jet, the Big Bunny, was a playground of scantily-clad, glorified housewives who were there to prioritise his pleasure above all else. Hefner's legacy is emblematic of how emancipatory movements - such as the pro-sex revolution - can be co-opted to self-serve the interests of those it seeks to challenge; exploitation becomes confused with liberation when only men define what a 'revolution' can be.

The iconic Playboy bunny - dressed in a skimpy corset, fluffy tail, stilettos and bunny ears - was, and still is, the ultimate caricature-esque symbol of female desirability. Hefner could usually be spotted with an army of bleach blonde devotees circled around him, while he often wore his trademark red silk pyjamas. Always ready and waiting to jump back into bed. As tributes roll in from women who have worked and played with him, an odd juxtaposition remains clear: women say they have been liberated by a man who used their sexuality and good looks to ‘release’ their inner stardom. It’s hard to count all the ways that feels so uncomfortable.

When feminist icon Gloria Steinem went undercover as a Playboy Bunny at one of Hefner’s Playboy Clubs, she wrote a scathing report on the rampant sexism and ill-treatment of women within this erotic dystopia. Men smoked cigars and drank fine whiskey while women lined up, always willing, to fulfill their greatest desires. Is this what the ‘sexual revolution’ looked like? Hefner admitted that he was a late bloomer - only masturbating for the first time aged 18, and losing his virginity at 22 - so one could argue that his life was one, huge mastubatory fantasy, not the sexual emancipation many claim it to be.

However, at the same time, writing Hefner off as just a sexist lech would be an oversimplification. His life took an increasingly seedy turn as it went on, and the idea of Hefner popping viagra every night to still get down and dirty with 20-something-year-olds became little more than a sleazy joke. If you were 'lucky' enough to get invited to the Playboy Mansion in Holmby Hills, you could expect little more than tits, booze and excess. And yet, as the world mourns the death of not just a man, but an ideology, it's hard not to feel a twinge of sadness at a passing era. Hefner was no civil rights hero, and he was no feminist ally, but he should be remembered as more than just a dirty old man. His doggy-style dogma embodied the unemcumbered ridiculousness of someone who didn't live by cultural norms. And didn't give a fuck what people thought.